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Issue 46, 2018
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Palladium-scavenging self-assembled hybrid hydrogels – reusable highly-active green catalysts for Suzuki–Miyaura cross-coupling reactions

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Abstract

A hybrid hydrogel based on 1,3:2,4-dibenzylidene sorbitol (DBS) modified with acyl hydrazides combined with agarose was used for in situ reduction and binding of palladium from aqueous mixtures without the need for an external reducing agent. Palladium uptake was monitored and the formation of Pd nanoparticles (PdNPs) trapped within the gel and located close to the nanofibres was confirmed. This gel effectively scavenges palladium from solution to concentrations < 0.04 ppm – well below the recommended limits for pharmaceutical products. The resulting hybrid hydrogel with embedded PdNPs was used as a catalyst for Suzuki–Miyaura cross-coupling reactions. The gel network stabilises PdNPs, preventing aggregation/leaching and giving excellent catalytic lifetimes. The gel acts as a simple reaction dosing form, being simply added to reactions performed in green solvents in air. Once reactions are complete, the gel can be simply removed, recycled and reused (>10 times). Reactions were purified by simple washing protocols, and leaching of Pd from the gels is limited (<1 ppm). The gels were also used in flow-through mode, giving efficient, rapid reactions, with easy work-up. These catalytic gels combine advantages of homogeneous and heterogeneous catalysts – they are solvent compatible with the reaction taking place in a solution-like environment, while the solid-like gel network enables catalyst recycling. In summary, these hydrogels scavenge ‘waste’ palladium and convert it into gel ‘wealth’ capable of efficient, environmentally-friendly Suzuki–Miyaura catalysis.

Graphical abstract: Palladium-scavenging self-assembled hybrid hydrogels – reusable highly-active green catalysts for Suzuki–Miyaura cross-coupling reactions

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Publication details

The article was received on 12 Oct 2018, accepted on 21 Oct 2018 and first published on 30 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC04561E
Citation: Chem. Sci., 2018,9, 8673-8681
  • Open access: Creative Commons BY license
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    Palladium-scavenging self-assembled hybrid hydrogels – reusable highly-active green catalysts for Suzuki–Miyaura cross-coupling reactions

    P. Slavík, D. W. Kurka and D. K. Smith, Chem. Sci., 2018, 9, 8673
    DOI: 10.1039/C8SC04561E

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